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Rauser M, Schroeder S, Niggemann M. Cooperative Catalysis: Calcium and Camphorsulfonic Acid Catalyzed Cycloisomerization of Diynols. Chemistry. 2015;21(45):15929-33doi: 10.1002/chem.201503293.
Rauser, M., Schroeder, S., & Niggemann, M. (2015). Cooperative Catalysis: Calcium and Camphorsulfonic Acid Catalyzed Cycloisomerization of Diynols. Chemistry (Weinheim an der Bergstrasse, Germany), 21(45), 15929-33. https://doi.org/10.1002/chem.201503293
Rauser, Marian, et al. "Cooperative Catalysis: Calcium and Camphorsulfonic Acid Catalyzed Cycloisomerization of Diynols." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,45 (2015): 15929-33. doi: https://doi.org/10.1002/chem.201503293
Rauser M, Schroeder S, Niggemann M. Cooperative Catalysis: Calcium and Camphorsulfonic Acid Catalyzed Cycloisomerization of Diynols. Chemistry. 2015 Nov 02;21(45):15929-33. doi: 10.1002/chem.201503293. Epub 2015 Sep 25. PMID: 26403228.
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Chemistry. 2015 Nov 02;21(45):15929-33. doi: 10.1002/chem.201503293. Epub 2015 Sep 25.

Cooperative Catalysis: Calcium and Camphorsulfonic Acid Catalyzed Cycloisomerization of Diynols.

Chemistry (Weinheim an der Bergstrasse, Germany)

Marian Rauser, Sebastian Schroeder, Meike Niggemann

Affiliations

  1. Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany).
  2. Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany). [email protected].

PMID: 26403228 DOI: 10.1002/chem.201503293

Abstract

The first transition metal-free cycloisomerization of easily accessible diynols is presented as a novel approach to bicyclic 2H-pyrans. As a one-step protocol, the reaction proceeds in a single reaction cascade by intertwining mechanistic fragments borrowed from transition metal-catalyzed Claisen rearrangment of vinyl ethers with our own work on allenyl/propargyl cation rearrangements and a 6π-oxo-electrocylization. It is enabled by a new cooperative catalytic system that combines a simple Ca(2+) catalyst with camphorsulfonic acid.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: calcium; cascade reactions; cooperative catalysis; cycloisomerization; electrocyclization

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